Issue 8, 2017

Dithieno[3,2-a:3′,2′-j][5,6,11,12]chrysene diimides and their molecular energy level regulation

Abstract

Dithieno[3,2-a:3′,2′-j][5,6,11,12]chrysene diimides (DTCDIs), a new class of organic dyes, with a twisted molecular backbone were designed and synthesized. The optical and electrochemical properties, charge transport behaviors and the single crystal structure were investigated. The cyanation of the DTCDI backbone was carried out to fine-tune the molecular energy levels. The addition of two cyano groups to the DTCDI backbone reduced the HOMO and LUMO energy levels by 0.35 and 0.30 eV, respectively. The energy levels could be further reduced with the addition of two more cyano groups leading to 0.32 and 0.22 eV reductions in HOMO and LUMO energy levels and stabilization of the energy levels. A tetracyano-substituted DTCDI derivative showed an electron mobility of 0.25 cm2 V−1 s−1 and a current on/off ratio of 106 in its organic thin film transistors.

Graphical abstract: Dithieno[3,2-a:3′,2′-j][5,6,11,12]chrysene diimides and their molecular energy level regulation

Supplementary files

Article information

Article type
Research Article
Submitted
21 1 2017
Accepted
13 4 2017
First published
04 5 2017

Mater. Chem. Front., 2017,1, 1635-1640

Dithieno[3,2-a:3′,2′-j][5,6,11,12]chrysene diimides and their molecular energy level regulation

X. Zhao, C. Ge, X. Yang and X. Gao, Mater. Chem. Front., 2017, 1, 1635 DOI: 10.1039/C7QM00030H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements